Methyl iodide → 2-(1-Pyrrolidinylmethyl)benzenesulfonamide, methyl iodide salt

HRID 1153868Notes

Reaction equation

HRID 1153868 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:13]([NH2:16])(=[O:15])=[O:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:17][I:18]>C(#N)C>[I-:18].[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:13]([NH:16][CH3:17])(=[O:14])=[O:15])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 133646292-(Pyrrolidin-1-ylmethyl)benzenesulfonamide

Product 1

HCID 1317139882-(1-Pyrrolidinylmethyl)benzenesulfonamide, methyl iodide salt

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(pyrrolidinomethyl)benzenesulfonamide (0.8 g) in acetonitrile (10 ml) was contacted with methyl iodide (3 ml) and heated to reflux for 2.0 hrs. Solvent was removed and the residue was treated with acetone and ether. The solid was filtered, digested with acetone (20 ml), chilled, and collected. There was obtained 1.00 g of white solid. 1H nmr δDMSO-d6TMS 8.15-7.30 (m), 5.07 (s, 2H), 3.9-3.3 (m, 4H), 2.90 (s, 3H), 2.4-1.8 (m 4H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2.0 hrs
  3. customSolvent was removed
  4. additionthe residue was treated with acetone and ether
  5. filtrationThe solid was filtered
  6. temperaturechilled
  7. customcollected

Sources & evidence

ORD record
ord-653b90ab6aab465c80b6f8a0f699fd6a
Source dataset
uspto-grants-1984_12
Patent number
US04486589

Reaction notes

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